117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless.
2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168
1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162
1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164
2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166
ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158
*Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.
The income description goes here to explain
| List Price | $350,000 |
| Property Type | Single Family Homes |
| Usable Sqft | 850 |
| Number of Stories | 0 stories |
| Parking Spots | 0 spots |
| Year Built | 1885 |
| Last Sold | Unknown |
| Sold Price | Unknown |
| Association Amenities: | Common Grounds,Extra Storage,Laundry Facilities,Picnic Area,Pier/Dock,Water/Lake Privileges,Reserved/Assigned Parking, Common Area Maintenance,Gas,Insurance,Water,Lawn Maintenance |
| APN # | 1504017927 |
| MLS # | MDKE2006168 |
| Property ID | 320363273 |
| Lot Sqft | Unknown |
| Zoning | RESIDENTIAL CONDOMINIUM |
| Days on Market | 66 |
| Original List Price | Unknown |
| Applicances | Washer,Dryer,Water Heater - Tankless% |
| Date Updated | April 16, 2026 |
| Date Created | February 28, 2026 |
Liddy Campbell an agent of . Lic #643182
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